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US8524439B2 - Silsesquioxane resin systems with base additives bearing electron-attracting functionalities - Google Patents

Silsesquioxane resin systems with base additives bearing electron-attracting functionalities Download PDF

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US8524439B2
US8524439B2 US12/304,263 US30426307A US8524439B2 US 8524439 B2 US8524439 B2 US 8524439B2 US 30426307 A US30426307 A US 30426307A US 8524439 B2 US8524439 B2 US 8524439B2
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bicyclo
composition
heptane
carboxylate
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US20090312467A1 (en
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Sanlin Hu
Eric Scott Moyer
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Tokyo Ohka Kogyo Co Ltd
Dow Silicones Corp
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Tokyo Ohka Kogyo Co Ltd
Dow Corning Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5435—Silicon-containing compounds containing oxygen containing oxygen in a ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1545—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups

Definitions

  • a good chemically amplified photoresist must meet all of the stringent requirements for microlithography at a given wavelength, such as transparent, chemically amplifiable, soluble in industry standard developer (e.g. tetramethyl ammonium hydroxide—TMAH), resistance to plasma etching, good adhesion to substrates, and exceptional thermal and mechanical properties for processing.
  • TMAH tetramethyl ammonium hydroxide
  • multi-layer processes such as tri-layer processes
  • SL thin single-layer
  • SL thin single-layer
  • the major challenge for the tri-layer process is to develop a hardmask layer which has not only high etch resistance, but also other matched optical properties both for the top-layer and the under-layer.
  • BL bi-layer
  • a thin top image layer usually a silicon-containing resist
  • ARC anti-reflective coating
  • the silicon-containing BL resist provides good etch selectivity for anisotropic etch processes, such as reactive ion etching (RIE) using an oxygen containing plasma.
  • RIE reactive ion etching
  • HSQ hydrogen silsesquioxane Due to its unique structure and high content of Si—H bonds, hydrogen silsesquioxane (HSQ) is remarkably transparent at 193 nm and 157 nm.
  • HSQ commercialized by Dow Corning under the trade name FOx®
  • FOx® spin-on low-k dielectric material
  • FOx® spin-on low-k dielectric material
  • TMAH tetra-methyl ammonium hydroxide
  • WO 2005/007747 which is hereby incorporated by reference, describes HSQ-based resins of the general formula (HSiO 3/2 ) a (RSiO 3/2 ) b wherein R is an acid dissociable group, a has a value of 0.2 to 0.9, b has a value of 0.1 to 0.8 and 0.9 ⁇ a+b ⁇ 1.0.
  • R is an acid dissociable group
  • a has a value of 0.2 to 0.9
  • b has a value of 0.1 to 0.8 and 0.9 ⁇ a+b ⁇ 1.0.
  • These HSQ-based resins are suitable as photoresists.
  • these resins have shown instability over time; therefore limiting their application.
  • This invention pertains to silsesquioxane-based compositions that contain
  • the 7-diethylamino-4-methylcoumarin stabilizes the silsesquioxane resin resulting in extended shelf life.
  • the compositions may be used in photoresist formulations.
  • the silsesquioxane resins can be, for example, those described in WO 2005/007747.
  • the silsesquioxane resins of this invention contain units of HSiO 3/2 and RSiO 3/2 wherein R is an acid dissociable group.
  • One such resin may have the formula (HSiO 3/2 ) a (RSiO 3/2 ) b where a has a value of 0.2 to 0.9, b has a value of 0.1 to 0.8 and 0.9 ⁇ a+b ⁇ 1.0.
  • a has a value of 0.4 to 0.8 and b has a value of 0.2 to 0.6.
  • the resists comprising the silsesquioxane resins of this invention have superior etch resistance, and low (or no) outgassing.
  • the silsesquioxane resin having the general formula (HSiO 3/2 ) a (RSiO 3/2 ) b (HSi(OR 1 )O 2/2 ) c wherein R, a and b are as described above and R 1 is selected from H or a linear or branched C 1 to C 6 alkyl group and c has a value of 0.01 to 0.4, alternatively 0.05 to 0.15, and 0.9 ⁇ a+b+c ⁇ 1.0. It is believed that the presence of HSi(OR 1 )O 2/2 units improves the adhesion of the resin to the substrate when the resin is used as a resist.
  • This invention also pertains to silsesquioxane resins having the general formula (HSiO 3/2 ) a (RSiO 3/2 ) b (Si(OR 1 ) x O (4-x)/2 ) d where R, R 1 , a and b are described above, d has a value of 0.05 to 0.45, alternatively 0.1 to 0.25, 0.9 ⁇ a+b+d ⁇ 1.0, and x has a value of 0 to 3. It is believed that the presence of Si(OR 1 ) x O (4-x)/2 units enhances the thermo-stability of the resin and affords higher Tg, and therefore improves the resist's resolution, contrast, line-edge roughness (LER), etc.
  • LER line-edge roughness
  • This invention also pertains to silsesquioxane resins having the general structure (HSiO 3/2 ) a (RSiO 3/2 ) b (R 2 SiO 3/2 ) e where R, a, and b are as described previously, R 2 is a property modifying functional group, e has a value of 0.01 to 0.25, alternatively 0.05 to 0.15 and, 0.9 ⁇ a+b+e ⁇ 1.0.
  • the R 2 group is used to modify properties such as the adhesion or Tg.
  • This invention also pertains to silsesquioxane resins having the general structure (HSiO 3/2 ) a (RSiO 3/2 ) b (HSi(OR 1 )O 2/2 ) c (R 2 SiO 3/2 ) e wherein R, R 1 , R 2 a, b, c and e are as described above and 0.9 ⁇ a+b+c+e ⁇ 1.0.
  • This invention also pertains to silsesquioxane resins having the general structure (HSiO 3/2 ) a (RSiO 3/2 ) b (Si(OR 1 ) x O (4-x)/2 ) d (R 2 SiO 3/2 ) e wherein R, R 1 , R 2 a, b, d, e and x are as described above and 0.9 ⁇ a+b+d+e ⁇ 1.0.
  • This invention also pertains to silsesquioxane resins having the general structure (HSiO 3/2 ) a (RSiO 3/2 ) b (HSi(OR 1 )O 2/2 ) c (Si(OR 1 ) x O (4-x)/2 ) d where R, R 1 , a, b, c, d, and x are described above and 0.9 ⁇ a+b+c+d ⁇ 1.0
  • This invention also pertains to silsesquioxane resins having the general structure (HSiO 3/2 ) a (RSiO 3/2 ) b (HSi(OR 1 )O 2/2 ) c (Si(OR 1 ) x O (4-x)/2 ) d (R 2 SiO 3/2 ) e where R, R 1 , R 2 a, b, c, d, e and x are described above and 0.9 ⁇ a+b+c+d+e ⁇ 1.0
  • silsesquioxane resins of this invention are not only highly transparent at low wavelength, but also satisfy numerous other requirements for a positive resist, such as adhesion, thermo-stability, chemically-amplifiable, aqueous-base solubility upon photo de-protection, and so on.
  • the silsesquioxane resins of this invention contain HSiO 3/2 units and RSiO 3/2 units where R is an acid dissociable group.
  • An “acid dissociable group” means a molecular moiety that is cleavable with acid, particularly photogenerated acid (PGA).
  • Acid dissociable groups are known in the art and are described, for example, in European Patent Application No. 1142928 and U.S. Patent Application Publication No. 2002/0090572, which are herein incorporated by reference for their teachings of acid dissociable groups. In particular, the acid dissociable groups can be described by the formula
  • each R 3 is independently a linking group
  • Each R 3 may be exemplified by, but not limited to, an alkylene group such as methylene and ethylene.
  • R 4 may be exemplified by, but not limited to, linear or branched alkylene groups, cycloalkylene groups such as norbornyl or cyclohexylene, fluoroalkylene groups, and aryl groups.
  • L may be exemplified by, but not limited to, substituted (e.g. fluorinated) and unsubstituted methylene, ethylene, norbornene, cycloalkylene and alkarylene moieties.
  • R 5 may be exemplified by, but not limited to, hydrogen, C 1 to C 6 alkyl groups such as methyl and ethyl and C 1 to C 6 fluoroalkyl groups such as trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoromethyl.
  • R 6 may be exemplified by, but not limited to, C 1 to C 6 alkyl groups such as methyl and ethyl and C 1 to C 6 fluoroalkyl groups such as trifluoromethyl, 2,2,2-trifluoroethyl and 3,3,3-trifluoropropyl.
  • Z may be exemplified by, but not limited to, —OH, —COOH, esters of the formula —COOR 7 , carbonates of the formula —OCOOR 8 , ethers of the formula —OR 9 , wherein R 7 , R 8 and R 9 are selected to render the functionality acid-cleavable.
  • R 7 may be a tertiary alkyl, e.g., t-butyl, a cyclic or alicyclic substituent (generally C 7 -C 12 ) with a tertiary attachment point such as adamantyl, norbornyl, isobornyl, 2-methyl-2-adamantyl, 2-methyl-2-isobornyl, 2-butyl-2-adamantyl, 2-propyl-2-isobornyl, 2-methyl-2-tetracyclododecenyl, 2-methyl-2-dihydrodicyclopentadienyl-cycl-ohexyl, 1-methylcyclopentyl or 1-methylcyclohexyl, or a 2-trialkylsilylethyl group, such as 2-trimethylsilyethyl, or 2-triethylsilylethyl.
  • a tertiary alkyl e.g., t-butyl,
  • Carbonate acid dissociable groups having the formula —OCOOR 8 may be exemplified by —O-t-butoxycarbonyl (i.e. R 8 is t-butyl).
  • Ether acid dissociable groups having the formula —OR 9 may be exemplified by tetrahydropyranyl ether (i.e. R 9 is tetrahydropyranyl) and trialkylsilyl ethers (i.e. R 9 is a trialkylsilyl such as trimethylsilyl).
  • Typical Z groups are organic ester groups that undergo a cleavage reaction in the presence of a photogenerated acid to generate a carboxylic acid group.
  • Acid dissociable groups, R may be exemplified by, but not limited to, 1,1-dimethylethyl, isopropyl, 2-methylkadamantyl, cyclohexyl, and 2-hydroxy-3-pinanyl or t-butyl ester of norbornane, and others.
  • the silsesquioxane resins may additionally contain HSi(OR 1 )O 2/2 units, or Si(OR 1 ) x O (4-x)/2 units, or (R 2 SiO 3/2 ) units or any combination of theses units to enhance the performance of the silsesquioxane resin.
  • each R 1 is independently selected from H or a C 1 to C 6 alkyl group.
  • R 1 may be exemplified by, but not limited to, methyl, ethyl, propyl, butyl, t-butyl and others. Typically R 1 is H or methyl.
  • R 2 is selected from the group consisting of moieties having the following structure —R 21 R 22 where R 22 is typically —OH or —COOH, or a base-soluble moiety, and R 21 is a substituted and/or unsubstituted C 1 to C 12 (linear, branched or cyclic) alkyl moieties.
  • R 2 may be exemplified by, but not limited to, bicyclo[2,2,1]hept-5-en-2-1,1,1-trifluoro-2-trifluoromethylpropan-2-ol; 2-trifluoromethyl bicyclo[2,2,1]hept-5-en-2-ol, 3,3,3-trifluoropropan-2-ol; and 2-trifluoromethyl-3,3-difluoro-bicyclo[2,2,1]hept-5-en-2-ol.
  • the silsesquioxane resin will contain 5 to 60 mole % of the HSi(OR 1 )O 2/2 units and more typically 5 to 45 mol % based on all units in the silsesquioxane resin. Additionally, the silsesquioxane resin may contain 5 to 45 mol % of Si(OR 1 ) x O (4-x)/2 units and more typically 10 to 25 mol % based on all units in the silsesquioxane resin. Further, the silsesquioxane resin may contain 0 to 25 mol % of (R 2 SiO 3/2 ) units, alternatively 10 to 15 mol % based on all units in the silsesquioxane resin.
  • silsesquioxane resins may be exemplified by but not limited to:
  • R is isopropyl, 2-methylkadamantyl, cyclohexyl, 2-hydroxy-3-pinanyl or t-butyl bicyclo[2,2,1]heptane-2-carboxylate;
  • R 1 is H;
  • a has a value of 0.5 to 0.7;
  • b has a value of 0.2 to 0.45;
  • c has a value of 0.05 to 0.2; and
  • d has a value of 0.01 to 0.1
  • R is isopropyl, 2-methylkadamantyl, cyclohexyl, 2-hydroxy-3-pinanyl or t-butyl bicyclo[2,2,1]heptane-2-carboxylate;
  • R 1 is H;
  • R 2 is bicyclo[2,2,1]hept-5-en-2-1,1,1-trifluoro-2-trifluoromethylpropan-2-ol, 2-trifluoromethyl bicyclo[2,2,1]hept-5-en-2-ol, 3,3,3-trifluoropropan-2-ol, 2-trifluoromethyl-3,3-difluoro-bicyclo[2,2,1]hept-5-en-2-ol;
  • a has a value of 0.4 to 0.6;
  • silsesquioxane resins of this invention may be prepared by reacting
  • Methods for preparing hydrogen silsesquioxane resins are known in the art.
  • One method involves the hydrolysis of trihalosilanes, such as trichlorosilane, or trialkoxysilanes, such as triethoxysilane.
  • Methods for preparing hydrogen silsesquioxane resins may be found in, but are not limited to, U.S. Pat. No. 3,615,272 to Collins et al., U.S. Pat. No. 5,010,159 to Bank et al., U.S. Pat. No. 4,999,397 to Frye et al., U.S. Pat. No. 6,353,074 to Carpenter et al., U.S. patent application Ser. No. 10/060,558 filed Jan. 30, 2002 and Japanese Patent Kokai Nos. 59-178749, 60-86017 and 63-107122.
  • the hydrogen silsesquioxane resin is reacted with (B) an acid dissociable group precursor.
  • One method for reacting the hydrogen silsesquioxane resin and acid dissociable group precursor comprises the catalytic hydrosilylation of the acid dissociable group precursor and hydrogen silsesquioxane resin.
  • Acid dissociable group precursors may be exemplified by, but not limited to, t-butyl ester of norbornene, t-butyl 2-trifluoromethyl acrylate, bicyclo[2,2,1]hept-5-en-2-t-butylcarboxylate, cis-5-norbornene-2,3-dicarboxylic anhydride, and others.
  • the amount of acid dissociable group precursor is added in an amount to provide 5 to 60 mole % of RSiO 3/2 units in the silsesquioxane resin based on all units in the silsesquioxane resin, alternatively 15 to 35 mol %.
  • Hydrosilylation catalysts are well known in the art and may be exemplified by, but not limited to, platinum-, nickel- or rhodium-containing compounds.
  • platinum-containing compounds include H 2 PtCl 6 , di- ⁇ -carbonyldi- ⁇ -cyclopentadienyldinickel, a platinum-carbonyl complex, a platinum-divinyltetramethyldisiloxane complex, a platinum cyclovinylmethylsiloxane complex and platinum acetylacetonate (acac).
  • An example of a rhodium-containing compound is Rh(acac) 2 (CO) 2
  • an example of a nickel-containing compound is Ni(acac) 2 .
  • the amount of hydrosilylation catalyst used is in the amount of 10 to 10,000 ppm, alternatively 100 to 1,000 ppm, based on the amount of reactants (i.e., hydrogen silsesquioxane resin and acid dissociable group precursor).
  • the reaction between the hydrogen silsesquioxane resin and acid dissociable group precursor is typically carried out at room temperature and ambient pressure, although heat or pressure may be used to facilitate the reaction.
  • the reaction between the hydrogen silsesquioxane and the acid dissociable group precursor is typically carried out in the presence of a solvent.
  • the solvent may be exemplified by, but not limited to, alcohols, such as ethyl alcohol or isopropyl alcohol; aromatic hydrocarbons, such as benzene or toluene; alkanes, such as n-heptane, dodecane or nonane; ketones, such as methyl iso-butyl ketone; esters; glycol ethers; siloxanes, such as cyclic dimethylpolysiloxanes and linear dimethylpolysiloxanes (e.g., hexamethyldisiloxane, octamethyltrisiloxane and mixtures thereof), 2-ethoxyethanol, propylene glycol methyl ether acetate (PGMEA), cyclohexanone, and 1,2-diethoxyethane, and others.
  • the reaction between the hydrogen silsesquioxane resin and acid dissociable group precursor is typically carried out for a time sufficient to react essentially all of the acid dissociable group precursor with the hydrogen silsesquioxane resin.
  • the reaction may be carried out for an extended period of time with heating from 40° C. up to the reflux temperature of the solvent (“bodying step”).
  • bodying step may be carried out subsequent to the reaction step or as part of the reaction step.
  • the bodying step is carried out for a period of time in the range of 30 minutes to 6 hours, more preferably 1 to 3 hours.
  • Silsesquioxane resins containing R 2 SiO 3/2 units are prepared by reacting the hydrogen silsesquioxane resin (A) or silsesquioxane resin (C) with a functional group precursor.
  • the hydrogen silsesquioxane resin or silsesquioxane resin is reacted with the functional group precursor by catalytic hydrosilylation of the functional group precursor and hydrogen silsesquioxane resin or silsesquioxane resin.
  • the catalytic hydrosilylation reaction is carried out using the same or similar process conditions as those described above for the catalytic hydrosilylation reaction between the hydrogen silsesquioxane resin and acid dissociable group precursor.
  • the hydrogen silsesquioxane resin (A) may reacted with the functional group precursor to produce a resin having the formula (HSiO 3/2 ) m1 (R 2 SiO 3/2 ) m3 (HSi(OR 1 )O 2/2 ) n (Si(OR 1 ) x O (4-x)/2 ) p where R 1 , n, p and x are as described previously; R 2 is a property modifying functional group; m3 has a value of 0.01 to 0.25, typically 0.05 to 0.15; and m1+m3 ⁇ m.
  • This resin is then reacted with the acid dissociable group precursor to produce a resin having the formula (HSiO 3/2 ) m1 (RSiO 3/2 ) m2 (R 2 SiO 3/2 ) m3 (HSi(OR 1 )O 2/2 ) n (Si(OR 1 ) x O (4-x)/2 ) p where R, R 1 , R 2 , n, p, m1, m2, m3 and x are as described previously and m1+m2+m3 ⁇ m.
  • the silsesquioxane resin (C) may be reacted with the functional group precursor to produce a resin have the formula (HSiO 3/2 ) m1 (RSiO 3/2 ) m2 (R 2 SiO 3/2 ) m3 (HSi(OR 1 )O 2/2 ) n (Si(OR 1 ) x O (4-x)/2 ) p where R, R 1 , R 2 , n, p, m1, m2, m3 and x are as described previously and m1+m2+m3 ⁇ m.
  • the hydrogen silsesquioxane resin (A) may be reacted with a mixture comprising both the functional group precursor and acid dissociable group precursor to produce a resin having the formula (HSiO 3/2 ) m1 (RSiO 3/2 ) m2 (R 2 SiO 3/2 ) m3 (HSi(OR 1 )O 2/2 ) n (Si(OR 1 ) x O (4-x)/2 ) p where R, R 1 , R 2 , n, p, m1, m2, m3 and x are as described previously and m1+m2+m3 ⁇ m.
  • the hydrogen silsesquioxane resin is reacted with the acid dissociable group precursor and the silsesquioxane resin is reacted with the functional group precursor.
  • novel functionalized hydrogen silsesquioxane-based resins of the present invention have a weight average molecular weight of about 500 to 100,000, preferably about 1,500 to 50,000, and more preferably about 2,000 to 30,000.
  • the novel functionalized hydrogen silsesquioxane resins of the present invention have adequate thermal stability, or more specifically a proper glass transition temperature (Tg) that is adequate for photoresist processing, such as post apply baking (PAB) and post-exposure baking (PEB).
  • Tg glass transition temperature
  • PAB post apply baking
  • PEB post-exposure baking
  • the Tg for the functionalized hydrogen silsesquioxane resins of the present invention is preferably 50 to 250° C., more preferably 70 to 180° C., and most preferably 80 to 150° C.
  • Another embodiment of this invention is a photoresist composition
  • a photoresist composition comprising (A) the silsesquioxane resins and 7-diethylamino-4-methylcoumarin described herein and (B) one or more acid generators.
  • the photoresist may take the form of a negative or a positive photoresist and other components and additives may be present.
  • the silsesquioxane resin is present in the photoresist composition in an amount up to 99.5 wt. % and the acid generator in an amount of 0.5-10 wt. %, based on the solids contained in the composition.
  • the acid generator is a compound that generates acid upon exposure to radiation. This acid then causes the acid dissociable group in the silsesquioxane resin to dissociate. Acid generators are well known in the art and are described in, for example, EP 1 142 928 A1. Acid generators may be exemplified by, but not limited to, onium salts, halogen-containing compounds, diazoketone compounds, sulfone compounds, sulfonate compounds and others.
  • onium salts include, but are not limited to, iodonium salts, sulfonium salts (including tetrahydrothiophenium salts), phosphonium salts, diazonium salts, and pyridinium salts.
  • halogen-containing compounds include, but are not limited to, mahaloalkyl group-containing hydrocarbon compounds, haloalkyl group-containing heterocyclic compounds, and others.
  • diazoketone compounds include, but are not limited to, 1,3-diketo-2-diazo compounds, diazobenzoquinone compounds, diazonaphthoquinone compounds, and others.
  • sulfone compounds include, but are not limited to, ⁇ -ketosulfone, ⁇ -sulfonylsulfone, ⁇ -diazo compounds of these compounds, and others.
  • sulfonate compounds include, but are not limited to, alkyl sulfonate, alkylimide sulfonate, haloalkyl sulfonate, aryl sulfonate, imino sulfonate, and others.
  • the preferred acid generators are sulfonated salts, in particular sulfonated salts with perfluorinated methide anions.
  • the photoresist composition may include organic base additives (or quenchers as acid-diffusion controllers), surfactants, dissolution inhibitors, cross-linking agents, sensitizers, halation inhibitors, adhesion promoters, storage stabilizers, anti-foaming agents, coating aids, plasticizers and others.
  • organic base additives or quenchers as acid-diffusion controllers
  • surfactants or quenchers as acid-diffusion controllers
  • dissolution inhibitors such as acid-diffusion controllers
  • cross-linking agents such as sensitizers, halation inhibitors, adhesion promoters, storage stabilizers, anti-foaming agents, coating aids, plasticizers and others.
  • the sum of all additives (not including the acid generator) will comprise less than 20 percent of the solids included in the photoresist composition, alternatively less than 5 percent.
  • the silsesquioxane-based compositions are delivered in a solvent.
  • solvent is governed by many factors, such as the solubility and miscibility of the silsesquioxane resin and 7-diethylamino-4-methylcoumarin, and safety and environmental regulations.
  • Typical solvents include ether-, ester-, hydroxyl- and ketone-containing compounds.
  • solvents include, but are not limited to, cyclopentanone, cyclohexanone, lactate esters such as ethyl lactate, alkylene glycol alkyl ether esters such as propylene glycol methyl ether acetate, alkylene glycol monoalkyl esters such as methyl cellusolve, butyl acetate, 2-ethoxyethanol, and ethyl 3-ethoxypropionate.
  • solvents for silsesquioxane resins include, but are not limited to, cyclopentanone (CP), propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), ethyl 3-tethoxypropionate, methyl n-amyl ketone (MAK) and any their mixtures.
  • CP cyclopentanone
  • PMEA propylene glycol methyl ether acetate
  • EL ethyl lactate
  • MIBK methyl isobutyl ketone
  • MEK methyl ethyl ketone
  • MAK ethyl 3-tethoxypropionate
  • the amount of solvent is typically present in an amount of 50 to 99.5 wt % based on the total weight of the silsesquioxane based composition, alternatively 80 to 95 wt %.
  • TSAM toluenesulfonic acid monohydrate
  • olefin solution was separately prepared by mixing ⁇ 0.1 mole of t-butyl 2-trifluoromethyl acrylate (TBTFMA) with anhydrate toluene (50:50). To this mixture ⁇ 200 ppm 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane complex (platinum, concentrated) was added.
  • TBTFMA t-butyl 2-trifluoromethyl acrylate
  • the olefin solution was charged into a flask equipped with a water condenser, thermometer, magnetic stir bar, and nitrogen bubbler. After purging with nitrogen, the HSQ solution prepared in Example 1 (containing ⁇ 0.33 mole of HSQ solid) was slowly added into the olefin solution. After the addition, the system was refluxed for approximately 4 hours while stirring moderately. The hydrosilylation reaction was monitored using 1H NMR until the olefin peaks disappeared completely.
  • Final resin solutions with a solid content ranging from 4 to 45 wt % were prepared by solvent exchange to a desired solvent, such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • a desired solvent such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • PMEA propylene glycol methyl ether acetate
  • EL ethyl lactate
  • MIBK methyl isobutyl ketone
  • An olefin solution was separately prepared by mixing approximately 0.1 moles of bicyclo[2,2,1]hept-5-ene-2-t-butylcarboxylate with anhydrate toluene (50:50). To this mixture 200 ppm 1,3-diethenyl-1,1,3,3-tetramenthyldisiloxane complex (platinum, concentrated) was added.
  • the olefin solution was charged into a flask equipped with a water condenser, thermometer, magnetic stir bar, and nitrogen bubbler. After purging with nitrogen, the HSQ solution prepared in Example 1 (containing ⁇ 0.33 mole of HSQ) was slowly added into the olefin solution. After the addition, the system was refluxed for 8 hours while stirring moderately. The hydrosilylation reaction was monitored using 1H NMR until the olefin peaks disappeared completely.
  • the final resin solution with a solid content ranging from 4 to 45 wt % was prepared by either solvent exchange to a desired solvent, such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • a desired solvent such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • An olefin solution was separately prepared by mixing ⁇ 0.10 mole of cis-5-Norbornene-2,3-dicarboxylic anhydride with anhydrate toluene (50:50). To this mixture ⁇ 200 ppm 1,3-diethenyl-1,1,3,3-tetramenthyldisiloxane complex (platinum-concentrated) was added.
  • the olefin solution was charged into a flask equipped with a water condenser, thermometer, magnetic stir bar, and nitrogen bubbler. After purging with nitrogen, the HSQ solution prepared in Example 1 (containing ⁇ 0.33 mole of HSQ,) was slowly added into the olefin solution. After the addition, the system was refluxed for 3 hours while stirring moderately. The hydrosilylation reaction was monitored using 1H NMR until the olefin peaks disappeared completely.
  • the final resin solution with a solid content ranging from 4 to 45 wt % was prepared by either solvent exchange to a desired solvent, such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • a desired solvent such as propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl isobutyl ketone (MIBK).
  • a photoresist composition was prepared by mixing until homogeneous: 15 parts silsesquioxane resin prepared in Example 3, 0.3 parts photoacid generator, either (C 6 H 5 ) 3 S + SbF 6 ⁇ or (p-(CH 3 ) 3 CC 6 H 4 ) 3 C ⁇ (SO 2 CF 3 ) 3 obtained from 3M), 84.7 parts PGMEA (electronic grade from General Chemical). Additionally about 0.01 parts of the organic base: 7-diethylamino-4-methylcoumarin, was added to the solution above.
  • the formulated photoresist solution was filtered through a 0.2 micron syringe filter, and then spin-coated onto a 6′′ silicon wafer.
  • the coated wafer was baked at 130° C. for 60 seconds before exposure at 248 nm or 193 nm with dose ranged from 8 to 100 mJ/cm 2 .
  • the film was then baked at 130° C. for 90 seconds, and developed with 0.263 N tetra-methyl ammonium hydroxide (MF CD26 from Shipley). High-resolution positive images with high contrast and low line-edge roughness (LER) were obtained. Additionally, the chemical stability (i.e., the resist shelf-life) and the CD stability of the formulated photoresist demonstrated significant improvement.

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WO2017192349A1 (fr) 2016-05-03 2017-11-09 Dow Corning Corporation Résine de silsesquioxane et composition d'anhydride de silyle
US10990012B2 (en) 2016-05-03 2021-04-27 Dow Silicones Corporation Silsesquioxane resin and oxaamine composition
US11370888B2 (en) 2016-06-16 2022-06-28 Dow Silicones Corporation Silicon-rich silsesquioxane resins

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WO2008002975A2 (fr) * 2006-06-28 2008-01-03 Dow Corning Corporation systèmes en résine de SILSESQUIOXANE avec additifs de base portant des fonctionnalités attirant les électrons
JP4890153B2 (ja) * 2006-08-11 2012-03-07 東京応化工業株式会社 レジスト組成物およびレジストパターン形成方法
JPWO2009096420A1 (ja) * 2008-01-31 2011-05-26 昭和電工株式会社 凹凸パターン形成方法、およびそれを利用した磁気記録媒体の製造方法
US8241707B2 (en) * 2008-03-05 2012-08-14 Dow Corning Corporation Silsesquioxane resins
KR101295858B1 (ko) * 2009-07-23 2013-08-12 다우 코닝 코포레이션 더블 패터닝 방법 및 물질
CN102439069B (zh) * 2009-07-23 2014-11-05 道康宁公司 用于反向图案化的方法和材料
JP5610567B2 (ja) * 2010-02-23 2014-10-22 昭和電工株式会社 レジスト感度向上方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017192349A1 (fr) 2016-05-03 2017-11-09 Dow Corning Corporation Résine de silsesquioxane et composition d'anhydride de silyle
US10990012B2 (en) 2016-05-03 2021-04-27 Dow Silicones Corporation Silsesquioxane resin and oxaamine composition
US11370888B2 (en) 2016-06-16 2022-06-28 Dow Silicones Corporation Silicon-rich silsesquioxane resins

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JP5085649B2 (ja) 2012-11-28
KR101216060B1 (ko) 2012-12-28
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